CA2287079C - Epoxidation process using improved heterogeneous catalyst composition - Google Patents

Epoxidation process using improved heterogeneous catalyst composition Download PDF

Info

Publication number: CA2287079C
Authority: CA; Canada
Prior art keywords: epoxidation process; catalyst composition; catalyst; silica; hydrocarbon solvent
Prior art date: 1997-05-05
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA002287079A

Other languages

English (en)

French (fr)

Other versions

CA2287079A1 (en

Inventor

Yuan-Zhang Han

Kevin M. Carroll

Edrick Morales

Robert G. Gastinger

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Lyondell Chemical Technology LP

Original Assignee

Arco Chemical Technology LP

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-05-05

Filing date

1998-05-04

Publication date

2007-10-02

1998-04-15 Priority claimed from US09/060,375 external-priority patent/US6011162A/en

1998-05-04 Application filed by Arco Chemical Technology LP filed Critical Arco Chemical Technology LP

1998-11-12 Publication of CA2287079A1 publication Critical patent/CA2287079A1/en

2007-10-02 Application granted granted Critical

2007-10-02 Publication of CA2287079C publication Critical patent/CA2287079C/en

2018-05-04 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000006735 epoxidation reaction Methods 0.000 title claims abstract description 58
238000000034 method Methods 0.000 title claims description 103
239000000203 mixture Substances 0.000 title claims description 62
230000008569 process Effects 0.000 title claims description 36
239000002638 heterogeneous catalyst Substances 0.000 title abstract description 5
239000003054 catalyst Substances 0.000 claims abstract description 137
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 79
238000001354 calcination Methods 0.000 claims abstract description 57
239000010936 titanium Substances 0.000 claims abstract description 56
239000002904 solvent Substances 0.000 claims abstract description 54
229910052719 titanium Inorganic materials 0.000 claims abstract description 52
229930195733 hydrocarbon Natural products 0.000 claims abstract description 39
150000002430 hydrocarbons Chemical class 0.000 claims abstract description 38
239000000377 silicon dioxide Substances 0.000 claims abstract description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 35
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 34
-1 titanium halide Chemical class 0.000 claims abstract description 32
150000001336 alkenes Chemical class 0.000 claims abstract description 14
150000002432 hydroperoxides Chemical class 0.000 claims abstract description 13
239000007787 solid Substances 0.000 claims description 40
238000005470 impregnation Methods 0.000 claims description 31
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 28
239000001301 oxygen Substances 0.000 claims description 28
229910052760 oxygen Inorganic materials 0.000 claims description 28
239000003795 chemical substances by application Substances 0.000 claims description 21
239000007789 gas Substances 0.000 claims description 20
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 15
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical group Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 13
GQNOPVSQPBUJKQ-UHFFFAOYSA-N 1-hydroperoxyethylbenzene Chemical group OOC(C)C1=CC=CC=C1 GQNOPVSQPBUJKQ-UHFFFAOYSA-N 0.000 claims description 12
238000010438 heat treatment Methods 0.000 claims description 12
238000001035 drying Methods 0.000 claims description 8
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 7
229910002091 carbon monoxide Inorganic materials 0.000 claims description 7
230000007717 exclusion Effects 0.000 claims description 7
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 6
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
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150000001282 organosilanes Chemical class 0.000 claims description 3
239000012018 catalyst precursor Substances 0.000 claims 9
239000000463 material Substances 0.000 abstract description 10
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239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
239000003863 metallic catalyst Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
229910052754 neon Inorganic materials 0.000 description 1
GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
239000012430 organic reaction media Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
239000008188 pellet Substances 0.000 description 1
238000005453 pelletization Methods 0.000 description 1
YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
239000012071 phase Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
230000001698 pyrogenic effect Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
150000004756 silanes Chemical class 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
229910052814 silicon oxide Inorganic materials 0.000 description 1
239000005049 silicon tetrachloride Substances 0.000 description 1
ABTOQLMXBSRXSM-UHFFFAOYSA-N silicon tetrafluoride Chemical compound F[Si](F)(F)F ABTOQLMXBSRXSM-UHFFFAOYSA-N 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
XROWMBWRMNHXMF-UHFFFAOYSA-J titanium tetrafluoride Chemical compound [F-].[F-].[F-].[F-].[Ti+4] XROWMBWRMNHXMF-UHFFFAOYSA-J 0.000 description 1
NLLZTRMHNHVXJJ-UHFFFAOYSA-J titanium tetraiodide Chemical compound I[Ti](I)(I)I NLLZTRMHNHVXJJ-UHFFFAOYSA-J 0.000 description 1
VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
150000003623 transition metal compounds Chemical class 0.000 description 1
LAJGDBSSLQUXMC-UHFFFAOYSA-N trimethyl(nitro)silane Chemical compound C[Si](C)(C)[N+]([O-])=O LAJGDBSSLQUXMC-UHFFFAOYSA-N 0.000 description 1
239000010887 waste solvent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/19—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic hydroperoxides
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/063—Titanium; Oxides or hydroxides thereof
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/08—Silica
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/0201—Impregnation
- B01J37/0203—Impregnation the impregnation liquid containing organic compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Epoxy Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)

CA002287079A 1997-05-05 1998-05-04 Epoxidation process using improved heterogeneous catalyst composition Expired - Fee Related CA2287079C (en)

Applications Claiming Priority (7)

Application Number	Priority Date	Filing Date	Title
US85110597A	1997-05-05	1997-05-05
US08/851,105		1997-05-05
US90079497A	1997-07-25	1997-07-25
US08/900,794		1997-07-25
US09/060,375 US6011162A (en)	1997-05-05	1998-04-15	Epoxidation process using improved heterogeneous catalyst composition
US09/060,375		1998-04-15
PCT/EP1998/002681 WO1998050374A2 (en)	1997-05-05	1998-05-04	Epoxidation process using improved heterogeneous catalyst composition

Publications (2)

Publication Number	Publication Date
CA2287079A1 CA2287079A1 (en)	1998-11-12
CA2287079C true CA2287079C (en)	2007-10-02

Family

ID=27369829

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002287079A Expired - Fee Related CA2287079C (en)	1997-05-05	1998-05-04	Epoxidation process using improved heterogeneous catalyst composition

Country Status (11)

Country	Link
EP (1)	EP0984949B1 (de)
JP (1)	JP4251666B2 (de)
KR (1)	KR100592442B1 (de)
CN (1)	CN1128792C (de)
AU (1)	AU8103598A (de)
BR (1)	BR9809020A (de)
CA (1)	CA2287079C (de)
DE (1)	DE69822151T2 (de)
ES (1)	ES2213285T3 (de)
RU (1)	RU2181121C2 (de)
WO (1)	WO1998050374A2 (de)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6114552A (en) *	1999-09-28	2000-09-05	Arco Chemical Technology, L.P.	Heterogeneous epoxidation catalyst
MY131860A (en) *	2000-06-21	2007-09-28	Shell Int Research	Process for preparation of catalyst and use there of
JP2004525901A (ja) *	2001-02-19	2004-08-26	ロンザア−ゲ−	アセチルピリジンを製造するための方法および触媒
US7067673B2 (en)	2001-02-19	2006-06-27	Lonza Ag	Process and catalyst for the preparation of acetylpyridines
US6872679B2 (en) *	2002-09-20	2005-03-29	Arco Chemical Technology, L.P.	Heterogeneous catalyst regeneration
CN100548492C (zh) *	2002-12-02	2009-10-14	国际壳牌研究有限公司	制备环氧化催化剂的方法和制备环氧化物的方法
CA2508043A1 (en) *	2002-12-02	2004-06-17	Shell Internationale Research Maatschappij B.V.	Process for the preparation of epoxidation catalysts
US7294727B2 (en)	2002-12-02	2007-11-13	Shell Oil Company	Catalyst preparation
WO2005028101A1 (ja) *	2003-09-18	2005-03-31	Sumitomo Chemical Company, Limited	チタン含有珪素酸化物触媒の製造方法、該触媒およびこれを使用したオキシラン化合物の製造方法
JP2009535206A (ja) *	2006-05-02	2009-10-01	シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー	チタン触媒、これの調製およびエポキシ化反応におけるこれの使用
KR101799718B1 (ko)	2014-01-22	2017-11-20	라이온델 케미칼 테크놀로지, 엘.피.	에폭시화 촉매의 제조 방법
WO2016133891A1 (en) *	2015-02-17	2016-08-25	Lyondell Chemical Technology, L.P.	Epoxidation catalysts based on metal alkoxide pretreated supports
TWI594951B (zh) *	2016-06-14	2017-08-11	東聯化學股份有限公司	Preparation and Application of Titanium Oxide - containing Materials
CN107552031B (zh) *	2016-07-01	2020-12-11	东联化学股份有限公司	含钛氧化硅材料的制备方法及应用

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Publication number	Priority date	Publication date	Assignee	Title
US4367342A (en) *	1969-04-02	1983-01-04	Shell Oil Company	Olefin epoxidation
US4021454A (en) *	1971-08-19	1977-05-03	Shell Oil Company	Olefin epoxidation
SU510476A1 (ru) *	1974-07-22	1976-04-15	Институт Химии Башкирского Филиала Ан Ссср	Способ получени окисей циклических олефинов
DE3322745A1 (de) *	1983-06-24	1985-01-03	Basf Ag, 6700 Ludwigshafen	Verfahren zur herstellung von oxiranen
US5081267A (en) *	1989-10-05	1992-01-14	Arco Chemical Technology, Inc.	Epoxidation process
FR2704159B1 (fr) *	1993-04-22	1995-06-09	Atochem Elf Sa	Catalyseur solide à base de silice particulaire, comportant du titane, Procédé d'obtention, et utilisation dans l'époxydation d'oléfines.
JP3658790B2 (ja) *	1995-03-30	2005-06-08	住友化学株式会社	触媒及びオキシラン化合物の製造方法
FR2743061A1 (fr) *	1995-12-27	1997-07-04	Atochem Elf Sa	Procede d'obtention d'un solide a base de silice et de titane et utilisation de ce solide notamment dans l'epoxydation des olefines.

1998
- 1998-05-04 WO PCT/EP1998/002681 patent/WO1998050374A2/en not_active Ceased
- 1998-05-04 EP EP98930675A patent/EP0984949B1/de not_active Expired - Lifetime
- 1998-05-04 KR KR1019997010231A patent/KR100592442B1/ko not_active Expired - Lifetime
- 1998-05-04 AU AU81035/98A patent/AU8103598A/en not_active Abandoned
- 1998-05-04 CN CN98804642A patent/CN1128792C/zh not_active Expired - Lifetime
- 1998-05-04 BR BR9809020-8A patent/BR9809020A/pt not_active IP Right Cessation
- 1998-05-04 ES ES98930675T patent/ES2213285T3/es not_active Expired - Lifetime
- 1998-05-04 RU RU99125770/04A patent/RU2181121C2/ru active
- 1998-05-04 JP JP54774198A patent/JP4251666B2/ja not_active Expired - Lifetime
- 1998-05-04 CA CA002287079A patent/CA2287079C/en not_active Expired - Fee Related
- 1998-05-04 DE DE69822151T patent/DE69822151T2/de not_active Expired - Lifetime

Also Published As

Publication number	Publication date
WO1998050374A3 (en)	1999-02-11
DE69822151D1 (de)	2004-04-08
JP2002514218A (ja)	2002-05-14
JP4251666B2 (ja)	2009-04-08
KR20010012279A (ko)	2001-02-15
RU2181121C2 (ru)	2002-04-10
CA2287079A1 (en)	1998-11-12
EP0984949A2 (de)	2000-03-15
CN1254336A (zh)	2000-05-24
KR100592442B1 (ko)	2006-06-22
EP0984949B1 (de)	2004-03-03
ES2213285T3 (es)	2004-08-16
AU8103598A (en)	1998-11-27
DE69822151T2 (de)	2005-01-27
WO1998050374A2 (en)	1998-11-12
BR9809020A (pt)	2000-08-01
CN1128792C (zh)	2003-11-26

Legal Events

Date	Code	Title	Description
2003-03-06	EEER	Examination request
2011-05-04	MKLA	Lapsed
2023-05-26	MKLA	Lapsed	Effective date: 20110504

Publication	Publication Date	Title
US6011162A (en)	2000-01-04	Epoxidation process using improved heterogeneous catalyst composition
EP1218365B1 (de)	2004-11-10	Heterogener epoxidations-katalysator
JP2909911B2 (ja)	1999-06-23	オキシラン化合物の製造方法
CA2287079C (en)	2007-10-02	Epoxidation process using improved heterogeneous catalyst composition
KR100827943B1 (ko)	2008-05-13	티탄 함유 규소 산화물 촉매의 제조방법
EP1539346B1 (de)	2009-10-21	Regeneration eines heterogenen katalysators
KR101799718B1 (ko)	2017-11-20	에폭시화 촉매의 제조 방법
US5798313A (en)	1998-08-25	Heterogeneous catalyst regeneration
KR100693773B1 (ko)	2007-03-12	촉매성형체, 촉매성형체의 제조방법 및 옥시란 화합물의제조방법
JP4834982B2 (ja)	2011-12-14	チタン含有珪素酸化物触媒の製造方法及び触媒
KR100994428B1 (ko)	2010-11-16	지지된 니오븀 옥사이드 촉매를 이용한 에폭시화 방법
KR900004926B1 (ko)	1990-07-12	에피클로로히드린류의 제조방법
CA2240785C (en)	2005-05-17	Preparation of oxirane compounds with titanasilsesquioxane catalysts